2-(indole-1-yl)-ethyl methanesulfonate | 565458-07-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(indole-1-yl)-ethyl methanesulfonate
• 英文别名: 1-(2-Methylsulphonyloxyethyl)indole；2-indol-1-ylethyl methanesulfonate
• CAS: 565458-07-3
• 化学式: C₁₁H₁₃NO₃S
• 分子量: 239.295
• InChiKey: RYPSIJNIFFTUHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  56.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(indole-1-yl)-ethyl methanesulfonate 、 ethyl-{benzyl-[3-hydroxybenzyl]-amino}-acetate 在 四丁基溴化铵 potassium carbonate 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 17.0h， 以54%的产率得到ethyl-{benzyl-[3-(2-indol-1-yl-ethoxy)-benzyl]-amino}-acetate
  参考文献：
  名称：

  [EN] HETEROCYCLIC COMPOUNDS FOR THE TREATMENT OF HYPERLIPIDEMIA, DIABETES, OBESITY AND SIMILAR DISEASES
  [FR] NOUVEAUX COMPOSES HETEROCYCLIQUES

  摘要：

  公开号：

  WO2005049589A3
• 作为产物：
  描述：

  甲基磺酰氯 、 1H-吲哚-1-乙醇 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-(indole-1-yl)-ethyl methanesulfonate
  参考文献：
  名称：

  Synthesis of Heterocycle-linked Thioureas and Their Inhibitory Activities of NO Production in LPS Activated Macrophages

  摘要：

  合成了一系列的硫脲作为脂多糖激活的巨噬细胞中NO产生的抑制剂。我们研究了硫脲的亲脂基团和N取代基对活性的影响。含有苯氧噻嗪和咔唑的衍生物表现出比含有吲哚的硫脲更高的活性。亲脂尾和硫脲头之间适当的间隔，以及在硫脲的N3位置上的甲基取代基对NO产生的抑制效果有利。 在所制备的化合物中，含有苯氧噻嗪的衍生物2a是最有效的，其< TEX>$IC_{50}$值为< TEX>$2.32 {\mu}M$。RT-PCR分析表明，所制备的硫脲通过抑制iNOS mRNA表达来抑制NO的产生。

  DOI：

  10.5012/bkcs.2010.31.01.027

文献信息

• Design and Synthesis of Novel 1,3-Dioxane-2-carboxylic Acid Derivatives as PPAR&amp;#945;/&amp;#947; Dual Agonists
  作者：Harikishore Pingali、Mukul Jain、Shailesh Shah、Pankaj Makadia、Pandurang Zaware、Jeevankumar Jamili、Kalapatapu V.V.M. Sairam、Pravin Patil、Dinesh Suthar、Suresh Giri、Harilal Patel、Pankaj Patel

  DOI：10.2174/157018010791306533

  日期：2010.7.1

  1,3-dioxane carboxylic acid derivatives were prepared based on our previous studies directed towards identifying novel pharmacophore for the development of PPAR α/γ dual agonists. Based on the typical topology of PPAR agonists we focused our design approach on modifying lipophilic tail and prepared a series of compounds by replacing the oxazole moiety of our previously reported compound with optimized lipophilic groups. Compound 8a was found to be a weak PPAR activator but exhibited potent hypolipidemic and anti-hyperglycemic activities in vivo due to superior bioavailability, whereas 8f exhibited potent in vitro and invivo effects. The activity of 8f is further supported by molecular docking study.

  1,3- 二氧六环羧酸衍生物的制备基于我们之前的研究，这些研究旨在为 PPAR α/γ 双激动剂的开发确定新的药理基础。根据 PPAR 激动剂的典型拓扑结构，我们将设计方法的重点放在了亲脂性尾部的修饰上，并用优化的亲脂基团取代了之前报道的化合物中的噁唑分子，制备了一系列化合物。研究发现，化合物 8a 是一种弱 PPAR 激活剂，但由于其生物利用度较高，在体内表现出了强效的降血脂和降血糖活性，而 8f 则在体外和体内都表现出了强效作用。分子对接研究进一步证实了 8f 的活性。
• Pheny (alkyl)carboxylic acid derivatives and dionic phenylalkylheterocyclic derivatives and their use as medicines with serum glucose and/or serum lipid lowering activity
  申请人：Giannessi Fabio

  公开号：US20050032787A1

  公开（公告）日：2005-02-10

  Formula (I) compounds are described: Where the groups are as defined here below, and their use as medinies, particularly as serum glucose and serum lipid lowering agents. Said medicines are useful for the prophylaxis and treatment of diabetes, particularly type 2, and its complications, Syndrome X, the various forms of insulin resistance, and hyperlipidaemias, and present reduced side effects, and, particularly, reduced or no liver toxicity.

  描述了公式(I)化合物：其中各组如下所定义，并且它们的用途作为药物，特别是作为血清葡萄糖和血清脂质降低剂。所述药物对于预防和治疗糖尿病，特别是2型糖尿病及其并发症，综合征X，各种形式的胰岛素抵抗和高脂血症非常有用，并且具有减少的副作用，特别是减少或无肝毒性。
• Novel Heterocyclic Compounds
  申请人：Lohray Bhushan Braj

  公开号：US20070275956A1

  公开（公告）日：2007-11-29

  Disclosed are novel compounds of formula (I, having hypolipidaemic and hypocholesterolemic properties, their tautomeric forms, their pharmaceutically acceptable salts, their pharmaceutically acceptable solvates and pharmaceutically acceptable compositions containing them.

  本发明涉及一种具有降脂和降胆固醇性质的新化合物，其化学式为（I），其互变异构体，其药学上可接受的盐，其药学上可接受的溶剂和包含它们的药学上可接受的组合物。
• PHENY(ALKYL)CARBOXYLIC ACID DERIVATIVES AND DIONIC PHENYLALKYLHETEROCYCLIC DERIVATIVES AND THEIR USE AS MEDICINES WITH SERUM GLUCOSE AND/OR SERUM LIPID LOWERING ACTIVITY
  申请人：SIGMA-TAU IndustrieFarmaceutiche Riunite S.p.A.

  公开号：EP1465858A2

  公开（公告）日：2004-10-13
• [EN] PHENY(ALKYL)CARBOXYLIC ACID DERIVATIVES AND DIONIC PHENYLALKYLHETEROCYCLIC DERIVATIVES AND THEIR USE AS MEDICINES WITH SERUM GLUCOSE AND/OR SERUM LIPID LOWERING ACTIVITY<br/>[FR] DERIVES D'ACIDE PHENY(ALKYL)CARBOXYLIQUE ET DERIVES PHENYLALKYLHETEROCYCLIQUES DIONIQUES ET LEUR UTILISATION COMME MEDICAMENTS A ACTIVITE D'ABAISSEMENT DE NIVEAU DE GLUCOSE SERIQUE ET/OU LIPIDES SERIQUES
  申请人：SIGMA TAU IND FARMACEUTI

  公开号：WO2003059864A2

  公开（公告）日：2003-07-24

  Formula (I) compounds are described: Where the groups are as defined here below, and their use as medinies, particularly as serum glucose and serum lipid lowering agents. Said medicines are useful for the prophylaxis and treatment of diabetes, particularly type 2, and its complications, Syndrome X, the various forms of insulin resistance, and hyperlipidaemias, and present reduced side effects, and, particularly, reduced or no liver toxicity.